Carbohydrate-protein binding is a supramolecular recognition process that underpins myriad biological events. However, the precise conformational and configurational requirements for biomolecular recognition are often poorly understood, since such phenomena often occur in a strongly spatiotemporal manner. Photoswitchable glycoconjugates have emerged as promising investigational tools for probing carbohydrate-protein recognition and for controlling bacterial adhesion. Reversible photoisomerisation, in particular that of azobenzene glycoconjugates, has also been exploited as a promising strategy for controlling supramolecular self-assembly and macroscopic properties, thereby facilitating the development of light responsive carbohydrate-based materials. The following review will highlight the recent advances in the design and applications of photoswitchable glycoconjugates, paying particular attention to the application of light as a stimulus for modulating protein and cellular adhesion, amphiphilicity and supramolecular assembly of carbohydrate-based materials.